(5Z)-5-(4-(dimethylamino)benzylidene)-4-(4-(methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one | 1448458-89-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (5Z)-5-(4-(dimethylamino)benzylidene)-4-(4-(methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one
• 英文别名: (5Z)-5-[[4-(dimethylamino)phenyl]methylidene]-4-(4-methylsulfonylphenyl)-3-phenylfuran-2-one
• CAS: 1448458-89-6
• 化学式: C₂₆H₂₃NO₄S
• 分子量: 445.539
• InChiKey: HCHJQULAKUGVCE-QJOMJCCJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-甲硫基苯乙酮 在 硫酸 、 氢溴酸 、 双氧水 、 sodium carbonate 、 溶剂黄146 、 sodium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.58h， 生成 (5Z)-5-(4-(dimethylamino)benzylidene)-4-(4-(methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one
  参考文献：
  名称：

  Stereoselective synthesis and anti-proliferative effects on prostate cancer evaluation of 5-substituted-3,4-diphenylfuran-2-ones

  摘要：

  Series of 5-substituted-3,4-diphenylfuran-2-ones were stereoselectively prepared. Their potential anti-proliferative effects on prostate cancer and some of their cyclooxygenases (COXs) inhibitory activities were evaluated. Structure activity relationship (SAR) data, acquired by substituent modification at the para-position and ortho-position of the C-3 phenyl ring and 5-substituted modification of the central furanone, showed that 3-(2-chloro-phenyl)-4-(4-methanesulfonyl-phenyl)-5-(1-methoxy-ethyl)-5H-furan-2-one (13p) was the most potent compound and could effectively reduce the proliferation of prostate cancer cells (PC3 cell IC50 = 20 mu M; PD PCDNA cell IC50 = 5 mu M; PD SKP2 cell IC50 = 5 mu M; DU145 cell IC50 = 25 mu M). The cell cycle analysis for 13p in DU145 indicated that 13p may induce G1 phase arrest. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.04.062

文献信息

• Development of Rofecoxib-Based Fluorescent Probes and Investigations on Their Solvatochromism, AIE Activity, Mechanochromism, and COX-2-Targeted Bioimaging
  作者：Lijun Xie、Renfu Li、Biyun Zheng、Zuoxu Xie、Xuefen Fang、Yanqi Wang、Gregory D. Cuny、Zhenli Li、Bin Lin、Xueyuan Chen、Ming Hu

  DOI：10.1021/acs.analchem.1c01978

  日期：2021.9.7

  attractive fluorescence properties, such as tunable blue-red emission, solvatochromism, aggression-induced emission behavior, and mechanochromism. Notably, the emission of 2a16 can be switched between green-yellow in the crystalline state and red-orange in the amorphous state by grinding and fuming treatments. Furthermore, the highly fluorescent compound 2a16 (Φf = 0.94 in powder) displayed a much stronger

  Cyclooxygenase-2 (COX-2) 荧光探针是用于癌症早期诊断的有前途的工具。传统上，COX-2 探针的设计是通过一个灵活的接头连接两个部分，一个荧光团和一个 COX-2 结合单元。在此，通过整合方法将结合单元和荧光团合二为一，通过对罗非昔布的一步修饰，开发了一类新的 COX-2 特异性荧光探针。其中，几种新的罗非昔布类似物不仅表现出仍然有效的 COX-2 结合能力，而且还表现出有吸引力的荧光特性，如可调蓝红光发射、溶剂化变色、攻击诱导发射行为和机械致变色。值得注意的是，2a16的排放通过研磨和熏蒸处理，可以在结晶态的绿黄色和非晶态的红橙色之间切换。此外，与COX-2 表达最低的 RAW264.7 正常细胞相比，高荧光化合物2a16（粉末中的Φ f = 0.94）在过度表达 COX-2 的 HeLa 癌细胞中显示出更强的 COX-2 荧光成像。最重要的是，2a16可以通过靶向
• Stereoselective synthesis and anti-proliferative effects on prostate cancer evaluation of 5-substituted-3,4-diphenylfuran-2-ones
  作者：Gai-Zhi Liu、Hai-Wei Xu、Peng Wang、Zong-Tao Lin、Ying-Chao Duan、Jia-Xin Zheng、Hong-Min Liu

  DOI：10.1016/j.ejmech.2013.04.062

  日期：2013.7

  Series of 5-substituted-3,4-diphenylfuran-2-ones were stereoselectively prepared. Their potential anti-proliferative effects on prostate cancer and some of their cyclooxygenases (COXs) inhibitory activities were evaluated. Structure activity relationship (SAR) data, acquired by substituent modification at the para-position and ortho-position of the C-3 phenyl ring and 5-substituted modification of the central furanone, showed that 3-(2-chloro-phenyl)-4-(4-methanesulfonyl-phenyl)-5-(1-methoxy-ethyl)-5H-furan-2-one (13p) was the most potent compound and could effectively reduce the proliferation of prostate cancer cells (PC3 cell IC50 = 20 mu M; PD PCDNA cell IC50 = 5 mu M; PD SKP2 cell IC50 = 5 mu M; DU145 cell IC50 = 25 mu M). The cell cycle analysis for 13p in DU145 indicated that 13p may induce G1 phase arrest. (C) 2013 Elsevier Masson SAS. All rights reserved.